Hey, I just got back from Key West two weeks ago! The chickens are still everywhere--the city hired a Chicken Wrangler a while back, which failed miserably. So they still have free reign. Just be careful when yer walking/driving around though, 'cause they do have a tendency to wander onto the sidewalks, streets, etc.
Also, there's a place caled The Chicken Store on Duval that acts as a chicken refuge and human gift shop. If you ever wanted to find anything that says "I love Coc_s", that's your best bet.
If you have a chance, do the Original Ghost Tour (
http://www.hauntedtours.com, if you're into that kind of thing). I've been on it thrice, and it's always really fun and entertaining.
Capt. Tony's bar is located where the original Sloppy Joe's bar once stood (if that makes sense), and is a great place to play pool and look at the multitude of crap thumbtacked to the walls.
There's a three story building that houses the Bull bar (1st), the Whistle Bar (2nd), and the Garden of Eden (rooftop). Be aware: The Garden of Eden is CLOTHING OPTIONAL. Yeah. See, we didn't know that the first time we walked up the stairs to look at the city at night.
There's nothing quite like being unexpectedly greeted by buck naked Ernest Hemingway lookalikes (ahem, plural) resting themselves on leather barstools. I still scream at night sometimes.
Let's see, what else? Oh yeah, park your car somewhere and LEAVE IT. Parking sucks, and can be expensive. So try to park your car somewhere safe (off the main roads like Duval and Truman) and either walk or rent a bicylcle/moped. You shouldn't need to drive anyway, since it's a small island.
Have fun!